"You never know what worse luck your bad luck has saved you from," wrote Cormac McCarthy in No Country for Old Men. It's an interesting perspective, but one that's unlikely to have been shared by Eugène Christophe, a French cyclist who could scarcely have endured more misfortune in the Tour de France if he'd careered across the path of a clowder of black cats and under several ladders before smithereening the contents of a hall of mirrors. Despite being the first rider to wear the yellow jersey in the Tour de France, upon the garish garment's introduction in 1919, Christophe failed to win the race in 11 attempts, due in no small part to continued rotten luck that has at least earned him a reputation in the pantheon as one of the most unfortunate cyclists in Tour history. Indeed, short of actually plunging to his death after cycling over the edge of an Alpine ravine, it's difficult to imagine from what worse fate the chronic bad luck suffered by the bike-racer from Malakoff outside Paris could possibly have been saved.

Having failed to win the 1912 race for no other reason than that it was decided by a points system rather than time, Christophe would go on to lose the Tour from a seemingly unassailable position on no fewer than three separate occasions because of the same mechanical problem. Contesting his sport at a time when cyclists set off on epic stages in the early hours of the morning and had to complete their own repairs without assistance from anyone else, Le Vieux Gaulois (The Old Gaul) would miss out when well-placed to take overall victory in 1913, 1919 and 1922 due to a broken fork.

The most famous of these incidents was the first, on the mountainous 373km (373!) jaunt from Bayonne to Bagnères-de-Luchon that took in the Col d'Osquich, Col d'Aubisque, Col du Soulor, Col du Tourmalet, Col d'Aspin and Col de Peyresourde. In second place on general classification four minutes and five seconds behind the previous year's winner, Odile Defraye of Belgium, Christophe and his Peugeot team-mates set a blistering pace from the get-go and by the summit of the Tourmalet, 2,115m above sea level, (the same mountain on which Defraye would later abandon through exhaustion), the Frenchman was more than 18 minutes clear of his nearest rival on the road and looking set fair for overall victory in that year's Tour. It was not to be; on the descent, the forks on Christophe's bike snapped, although for years he would dishonestly claim he'd been hit by a car in order to save face for his employers, who were also the manufacturers of his machine. Shouldering his useless bike, the distraught Christophe proceeded to walk 14km to the nearest village.

"All the riders I had dropped during the climb soon caught me up," Christophe would later recall. "I was weeping with anger. As I walked down I was looking for a shortcut. I thought maybe one of the pack trails would lead me straight to Sainte-Marie-de-Campan, but I was weeping so badly I couldn't see anything. With my bike on my shoulder, I walked for more than 10km. On arriving in the village at Sainte-Marie-de-Campan, I met a young girl who led me to the blacksmith on the other side of the village. His name was Monsieur Lecomte."

Forbidden from receiving hands-on assistance from Monsieur Lecomte by the beady-eyed race officials who'd followed him down the Tourmalet, Christophe fixed his bike on the forge with the blacksmith instructing him from the sidelines. Having already lost two hours on his walk to the village, he finally finished the stage a whopping three hours and 50 minutes behind new race leader, the Belgian Philippe Thys, only to be told he was being penalised an additional 10 minutes because a seven-year-old boy had operated the bellows for him while he was repairing his bike. Peugeot immediately appealed against this comically merciless punishment and had Christophe's penalty reduced to three minutes. Thys went on to win the Tour that year, with Christophe finishing seventh on GC out of the 35 finishers (140 had started the race). Thirty years later, possibly as some sort of horrible joke, Peugeot would present the luckless cyclist with the very forks he'd repaired himself as a memento of a very long and difficult day the Frenchman would probably have preferred to forget. BG

It was the defeat that brought a great champion the acclaim that his victories had not. Jacques Anquetil came into the 1964 Tour de France having won the race for each of the previous three years, and four times overall, yet despite this success and his classic good looks the 30-year-old remained largely unloved by the general public.

France's heart belonged to Raymond Poulidor, who, though just two years younger, had only competed in the Tour twice, finishing third in 1962 and eighth in '63 – but his gutsy style enraptured the public in a way that the austere, calculating approach of Anquetil never did. In a race expressly designed to make riders suffer, Anquetil never betrayed any pain, always seemed in control, with his wins considered rewards for tactical shrewdness, helpful team-mates and excellence in time-trials rather than the more popular qualities embodied by Poulidor – power, aggression and courage. The public's desire to see the man they affectionally called Poupou prevail was increased after the ninth stage, when, after 239km, Poulidor arrived first at the Monaco velodrome … but forgot that he had to do a lap of it to complete the stage. Anquetil took advantage of Poulidor's mistake to win the stage instead and claim the one-minute bonus.

By the time they came to the final mountain stage, 217km from Brive to Puy-de-Dôme, Anquetil was still 56 seconds ahead of Poulidor in the GC. With just two plain stages and a time-trial to follow, this was considered the last chance for Poulidor, regarded as the far superior climber, to make a bid for Tour victory. He made his move on the final ascent. But Anquetil decided to try and match the more powerful man, pedal-for-pedal. For over 10km, at gradients reaching 13%, Anquetil rode right alongside Poulidor, the pair occasionally banging shoulders as Poulidor tried in vain to drop him. The half a million spectators lining the roads, and the viewers watching the Tour live on TV for the first time, were enthralled, their admiration for Anquetil increasing with every metre that he defied their expectations of him fading. Anquetil, the so-called automaton, was in agony – but he would not yield, becoming more human and more heroic with every metre that he kept up with the exasperated Poulidor. Only with 900 metres to go did Poulidor eventually escape but it was too late to make a significant dent in the overall lead.

Anquetil went on to secure his fifth Tour title. Poulidor, meanwhile, won 189 races in his career, including the Tour of Spain, but he is defined more by his close misses in the Tour de France, where he finished third five times and second three times, the eternal, ever-popular underdog. PD

One of the most steep and scenic of the Alpine climbs, the 11.6-kilometre Col de Joux-Plane has, in its time, made a folk hero of Marco Pantani, who famously climbed its 1,700m summit in 33 minutes while proving one of few mountains to get the better of Lance Armstrong. As it turned out, both men were almost certainly loaded on goof-balls on each occasion, but it seems unlikely that either can have been as off their heads while climbing it as Floyd Landis was when he broke away to win stage 17 and ostensibly the Tour de Tour de France in July 2006.

Having had the mother of all shockers in the mountains the previous day in a stage won by the Dane Michael Rasmussen, another serial doper who would be kicked off the following year's Tour in disgrace while in possession of the yellow jersey, Landis as good as conceded victory was beyond him when he fronted up before a gaggle of journalists for a good-humoured impromptu press conference in which he stated he wouldn't mind having a couple of beers.

Retiring to his hotel room afterwards, Landis did indeed get loaded, but his drug of choice was an epic amount of testosterone, rather than a six-pack of booze. The following day's stage boasted five categorised climbs and Landis began it more than 11 minutes behind race leader Oscar Pereiro, having held the lead by 10 seconds just 24 hours previously. With a breakaway of inconsequential riders having opened a gap early in the stage, Landis sent his Phonak team-mates to the front of the peloton, where they put the hammer down.

As nature took its course and the weaker riders were shelled out the back, the main focus of attention was the group of big name GC contenders and Landis, including Pereiro, Carlos Sastre, Andreas Klöden, Damiano Cunego and Cadel Evans. With 127 kilometres and five climbs to go, the American attacked off the front and his rivals let him go. Approximately 100 kilometres later they realised they'd made a terrible error, long after the panic-stricken maillot jaune Pereiro had pleaded in vain for some help reeling in Landis. Their late attempt to undo the damage done was in vain and the Phonak rider's testosterone-charged mountain assault enabled him to win the stage by a staggering 5min 42sec from Sastre and shoot back up to third place on GC, 30 seconds behind Pereiro.

At the time, it was regarded by some with suspicion, but many others as a heroic achievement; one of the great Tour rides that provided the likeable Landis with the platform from which to go on and win the race by 57 seconds from Pereira in the final time-trial. A week after his stage win, however, it was announced that the obligatory urine test given by Landis had tested positive for synthetic testosterone that put him three times over the hormonal limits permitted by World Anti-Doping Agency rules. When his 'B' test confirmed the findings, Landis was immediately sacked by Phonak despite the emphatic protestations of innocence from the rider, which turned out to be total cobblers, and he went on to be stripped of his Tour win and suspended in the most ignominious of circumstances. The most ignominious, that is, until those endured by his former team-mate Lance Armstrong, who Landis eventually took down with him. Simultaneously the best and worst day of Landis's career, it could be argued that Thursday 20 July 2006 was a black day for the sport of cycling, but the cyclist's failed test and subsequent fall-out mean it is also the date when the rehabilitation of a sport that was on its knees finally began what at least seems to be a welcome recovery. BG

4) Stage 13, 1951: Perpignan to Nîmes

As much about valiant failure as heroic victory (is finishing last in any other race considered a badge of honour?), the Tour de France has thrown up more than its fair share of tragicomic tales in its 100 editions, few more amusing than that of Abdel-Khader Zaaf, the man who famously went the wrong way.

Riding in stifling heat as 50% of a two-man breakaway with his team-mate and fellow North African Marcel Molines that began with 200 kilometres to go, Zaaf learned that they had opened a gap of more than 20 minutes on an apathetic peloton who let them escape because they were so far behind on GC. Excited to realise this would be enough to put him in the yellow jersey, Zaaf completely lost the run of himself, forgot to drink anything and began weaving around the road as a result of dehydration with less than 20 kilometres to go.

Eventually grabbing a bottle proffered by a concerned citizen standing roadside, Zaaf lowered the contents in one lengthy draft, but continued zigzagging hopelessly along the road in an apparent state of delirium, before falling off his bike and being dragged into the shade of a tree by a number of spectators, where he proceeded to fall asleep. It turned out Zaaf was drunk. Trousered. Banjoed. A teetotal Muslim, he'd only gone and grabbed a bottle of white wine from the hand of a well meaning stranger and never having had so much as a sniff of the cork before, he was left in a state of hopeless disrepair by the contents, which certainly left him refreshed, albeit not in the way he'd hoped.

Upon coming round some minutes later, a decidedly confused and tiddly Zaaf remounted his bicycle and set off in the wrong direction, prompting the spectators lining the route to summon an ambulance to bring the stricken rider to Nîmes. His pleas to be allowed to finish the closing 20 kilometres the following day fell on the deaf ears of jobsworth race officials and he was removed from the race for failing to finish a stage. His Tour was over, but the legend had just begun. BG

Only three riders were expected to seriously challenge for the maillot jaune in 1989: Pedro Delgado, Laurent Fignon, and Stephen Roche. Delgado was the hot favourite to win the 76th Tour, the reigning champion from Spain, but his race was effectively run before he'd pressed a pedal towards the floor. Stopping to sign some autographs while out on a warm-up run before the big off, he failed to give himself enough time to get back to the starting ramp, and when he finally did, found the clock had been spinning around for a whopping two minutes and 40 seconds. It was beyond farcical and, psychologically jiggered, his challenge never recovered. "I didn't notice time passing," sighed the foolish Delgado, but then again, who can live a life without saying that.

Meanwhile Roche, the 1987 winner from Ireland, soon aggravated long-standing problems with his left knee, and was eventually forced to withdraw a week in. A shoo-in for Fignon, then, a victory for France, and what a way to embellish the bicentenary celebrations of the French Revolution! Let them eat the icing on the cake!

Few considered the chances of Greg LeMond, who had become the first (and is still the only legit) American to win the tour in 1986. LeMond hadn't competed in Le Tour since that victory, having been accidentally peppered with buckshot by his uncle and brother-in-law while on a turkey shoot in 1987. While the incident reads like a particularly memorable Chuck Jones animation, it was an altogether more serious affair than mere ACME-product larks; LeMond nearly bled to death, pellets lodged in his heart, lungs and liver, and subsequently missed a large chunk of his career. Now he was happily fit again and back in the saddle, but little was expected of him this time round.

But the pressure was off, and LeMond delivered. After a win in the stage five time trial, he grabbed the lead in the GC. From that early point, it would be hand-to-hand combat with Fignon. The American, with Fignon struggling in the mountains, held a 53-second lead heading towards L'Alpe D'Huez on the 17th stage of 21, but the French rider launched a blistering attack 4km from the summit and ended the day with a 26-second advantage. With four stages remaining, Fignon then followed that devastating turnaround with what appeared to be a killer blow, winning his first stage with another well-timed attack, this time on the Côte de St Nizier-du-Moucherotte. Having built a 50-second lead in the GC so close to home, it looked done and dusted.

The two riders went into the final stage, the individual time trial between Versailles and Paris, with Fignon still 50 seconds ahead. LeMond, however, was racing with an aerodynamic helmet and triathlon-style handlebars. Fignon sported a distinctly non-supersonic ponytail and had a basket on his handlebars loaded down with hubris. Having reportedly congratulated LeMond on second place before the 25km time trial, he was shocked to see the American, going off one ahead of him, eat up his advantage: 21 seconds up at 11.5km, 24 ahead at 14, 29 in front at 18. As LeMond crossed the line at Champs Elysées, having ridden the fastest-ever Tour time trial at speeds touching 34mph, he heard the announcer say that Fignon had 20 seconds left to get to the line and win the Tour. "I saw him coming and thought the worst that could happen was that I lost the Tour by one second," said LeMond.

But Fignon could not make it, straining desperately but coming in eight seconds short before collapsing on to the floor in exhaustion and agony, both of the mental as well as physical kind. It was the shortest gap in Tour-winning history, and the biggest blow. LeMond took the garland as he celebrated perhaps the greatest comeback in all cycling. Poor Fignon, already unloved by many French pushbike fans for his measured, professorial style, had now buggered up the bicentennial celebrations and would be destined to live out the rest of his days, despite the two Tours he'd already won, as Monsieur Eight Seconds. "Winning and losing are never easy whatever the conditions," he later reflected ruefully, "but it can be worst of all if you lose in certain circumstances." SM